Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D17/00—Pigment pastes, e.g. for mixing in paints
  • C09D17/002—Pigment pastes, e.g. for mixing in paints in organic medium
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
  • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
  • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
  • C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
  • C08G12/12—Ureas; Thioureas
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G6/00—Condensation polymers of aldehydes or ketones only
  • C08G6/02—Condensation polymers of aldehydes or ketones only of aldehydes with ketones
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
  • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
  • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
  • C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
  • C09D161/02—Condensation polymers of aldehydes or ketones only
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/65—Additives macromolecular
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
  • C08L61/02—Condensation polymers of aldehydes or ketones only
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
  • Y10S525/934—Powdered coating composition
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/31504—Composite [nonstructural laminate]
  • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
  • Y10T428/31594—Next to aldehyde or ketone condensation product [phenol-aldehyde, etc.]

Definitions

• the invention relates to a ketone-aldehyde resin with wide compatibility, comprising cycloaliphatic ketones and, in particular, formaldehyde and, if desired, further monomers, to a process for its preparation and to compositions which use a hard resin, such as in paints, printing inks and other coatings, especially in pigment preparations.
• Tinting pastes based on cyclohexanone- or methylcyclohexanone-formaldehyde resins lead to instances of instability, especially in coating systems comprising binders and solvents of low polarity.
• EP-B 0 007 106 discloses polycondensation products of aliphatic and cyclic ketones, which, prepared by the process disclosed therein, have very high softening points and are therefore insoluble in aliphatic solvents.
• the object of the invention was to develop ketone-aldehyde resins with wide compatibility and a process for their preparation.
• the resin should be compatible with as wide as possible a spectra of coating binders. It should possess a solubility which is as universal as possible, with solubility in aliphatic compounds being a particular desire.
• the usual properties of ketone-aldehyde resins should be maintained and good pigment wetting should be ensured.
• ketone-formaldehyde resins which comprise cycloaliphatic ketones, aldehyde and, if desired, further monomers, these resins comprising
• ketones III 0 to 60 mol %, based on all of the ketones employed, of further ketones having aliphatic, cycloaliphatic or aromatic hydrocarbon radicals which may be substituted in the hydrocarbon chain by identical or different substituents and, in turn, by the above-mentioned hydrocarbon radicals, and, if desired, phenols and/or urea or its derivatives.
• Particularly preferred C 1 - to C 8 -alkyl-substituted cyclohexanones are 4-tert-butylcyclohexanone and 3,3,5-trimethylcyclohexanone.
• the ketone-aldehyde resins according to the invention have a broad solubility and compatibility and are particularly suitable for pigment preparations which are capable of universal application.
• the ketone-aldehyde resins according to the invention are soluble in virtually all coatings-relevant organic solvents, including in particular mineral oils, white spirits and aliphatic compounds. This provides the possibility of formulating low-odor, environmentally compatible and toxicologically harmless coating systems.
• the ketone-aldehyde resins have a wide compatibility with binders and resins. In particular they are miscible even with relatively non-polar types such as long-oil alkyd resins, natural oils, hydrocarbon resins and polyamides. They are therefore particularly suitable as a hard resin in paints and printing inks.
• ketone-aldehyde resin according to the invention it is possible to formulate stable pigment preparations and tinting pastes which can be employed in most coating systems and lead to outstanding color properties.
• the ketone-aldehyde resin according to the invention may comprise, individually or as a mixture, all alkyl-substituted cyclohexanones having one or more C 1-8 alkyl radicals.
• Examples which may be mentioned are 4-tert-amylcyclohexanone, 2-sec-butylcyclohexanone, 2-tert-butylcyclohexanone, 4-tert-butylcyclohexanone, 2-methylcyclohexanone and 3,3,5-trimethylcyclohexanone.
• 4-tert-butylcyclohexanone and 3,3,5-trimethylcyclohexanone are preferred.
• C 1-20 aliphatic aldehydes which are suitable in principle are unbranched or branched aldehydes such as, for example, formaldehyde, acetaldehyde, butyraldehyde, dodecanal, etc., although it is preferred to employ formaldehyde.
• formaldehyde required is usually employed as an approximately 30% strength by weight aqueous solution.
• other practical forms of formaldehyde are also possible.
• aromatic aldehydes such as benzaldehyde, for example, may be present in a mixture with formaldehyde.
• ketones which the ketone-aldehyde resins according to the invention may contain are, alone or in a mixture, preferably ketones of C 1-20 aliphatic, C 3-20 cycloaliphatic, C 6-30 aromatic or a mixture thereof. Examples which may be mentioned are acetone, methyl ethyl ketone, 3-pentanone, methyl isobutyl ketone, cyclopentanone, mixtures of 2,2,4- and 2,4,4-trimethylcyclopentanone, cyclohexanone, cycloheptanone and cyclooctanone.
• the further monomers is intended to exclude C 1-8 alkyl substituted cyclohexanones. Methyl ethyl ketone, cyclohexanone and acetophenone, however, are preferred. Generally, however, all ketones which are mentioned in the literature as being suitable for ketone resin syntheses can be employed.
• a particular embodiment of the invention comprises mixtures of cyclohexanones. Particular importance as regards performance is attached to mixtures of trimethylcyclohexanone/cyclohexanone, 4-tert-butyl cyclohexanone/trimethylcyclohexanone/cyclohexanone, and 4-tert-butylcyclohexanone/trimethylcyclohexanone.
• the ketone-aldehyde resins according to the invention preferably have an average molecular weight (Mn) in the range of from 500 to 1,000, particularly preferably from 500 to 800.
• Ketones and 1/3 of the required formaldehyde in the form of an approximately 30% strength by weight formalin solution are taken as initial charge in a conventional manner and are heated to 60° C. Then the required NaOH in the form of a 50% strength by weight aqueous solution is added dropwise over the course of 15 min and the mixture is heated to 80° C. Subsequently the remaining quantity of formalin is added dropwise over the course of 90 min and the mixture is held under reflux at about 85° C. for 4 hours. After addition of glacial acetic acid to the resin formed the latter is washed to neutrality with water. Distillation results in pale yellow, brittle resins with softening points of between 80° and 90° C.
• Resins 1 to 4 from Examples 1 to 4 were tested for their solubility in various solvents, in comparison with two commercially available cyclohexanone-formaldehyde resins.
• Resins 1 to 4 from Examples 1 to 4 were tested for their compatibility with various binders and resins, in comparison with two commercially available cyclohexanone-formaldehyde resins, in a weight ratio of ketone-formaldehyde resin/binder or resin of 40:60. To this end the substances were dissolved in suitable solvents, mixed and investigated for incompatibility (clouding, etc.) in the form of a dried film on glass.
• Resin 4 from Example 4 was used to prepare tinting pastes in various colors, in conventional manner.
• tinting pastes were completed to the coating material by adding 10 parts by weight of tinting paste to the alkyd resin paint listed below.
• the pastes could be admixed with the coating material without problems.
• the coating materials had good rheological properties and good flocculation stability.
• Paint films on sheet steel were prepared and assessed in the conventional manner.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Wood Science & Technology (AREA)
• Engineering & Computer Science (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Life Sciences & Earth Sciences (AREA)
• Materials Engineering (AREA)
• Phenolic Resins Or Amino Resins (AREA)
• Paints Or Removers (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Compounds Of Unknown Constitution (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Applications Claiming Priority (2)

Publications (1)

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Family Applications (1)

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Cited By (10)

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Citations (4)

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• 1994
  • 1994-02-16 DE DE4404809A patent/DE4404809A1/de not_active Withdrawn
  • 1994-12-17 ES ES94120048T patent/ES2123088T3/es not_active Expired - Lifetime
  • 1994-12-17 AT AT94120048T patent/ATE172473T1/de active
  • 1994-12-17 DE DE59407132T patent/DE59407132D1/de not_active Expired - Lifetime
  • 1994-12-17 EP EP19940120048 patent/EP0668301B1/de not_active Expired - Lifetime
• 1995
  • 1995-02-14 CA CA 2142524 patent/CA2142524A1/en not_active Abandoned
  • 1995-02-14 US US08/388,283 patent/US5705597A/en not_active Expired - Fee Related
  • 1995-02-15 AU AU12275/95A patent/AU690613B2/en not_active Ceased
  • 1995-02-15 CN CN95101895A patent/CN1048735C/zh not_active Expired - Fee Related
  • 1995-02-15 KR KR1019950002776A patent/KR950032344A/ko not_active Withdrawn
  • 1995-02-15 ZA ZA951215A patent/ZA951215B/xx unknown
  • 1995-02-15 JP JP2680495A patent/JPH07252338A/ja active Pending

Patent Citations (4)

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